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Celebrate Valentine’s Day in beautiful Key West!

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Key West Tours

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Have an adventure this Valentine’s Day in Key West with the one you love. Join Cool Key West for a perfect sunset sail, a romantic day sailing, snorkeling, and kayaking, or go all out with jet ski tour around the island.

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  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    5.0 (1,561)

    Key West Wind & Wine Sunset Sail

    Wind & Wine has been the #1 rated sunset sail on Cool Key West for over a decade. In our opinion, this is the best

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    $109
    $99
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,484)

    Key West Sail, Snorkel, Kayak with Sunset Option

    Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge.

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $99
    $90
    $99
    $90
  • Key West Original Island Jet Ski Tour
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,889)

    Key West Original Island Jet Ski Tour

    Enjoy exciting high-speed watersports fun with the best Key West jet ski tour – the Key West Original Island Jet Ski Tour, a guided 28-mile

     1 hour 30 minutes (approx.)  Free Cancellation  Instant Confirmation
    $159
    $99
    $159
    $99
  • Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
    Special Offer
    Special Offer
    4.9 (124)

    Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

    Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise

     2 hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    $99
    $89
  • Key West Deep Sea Fishing Charter
    Likely to Sell Out
    Likely to Sell Out
    4.9 (263)

    Key West Deep Sea Fishing Charter

    Cool Key West takes you on a Key West Deep Sea Fishing Charter for high adventure and big fish on the deep blue waters that

     4, 6 or 8 hours (approx.)  Free Cancellation
    $1,000
    $900
    $1,000
    $900
  • Key West Split Fishing Charter
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.8 (493)

    Key West Split Fishing Charter

    Cool Key West presents the Key West Split Fishing Charter: the most cost-effective and convenient way to get offshore and enjoy some Key West sportfishing.

     4 or 6 hours (approx.)  Free Cancellation
    $350
    $200
    $350
    $200
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  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
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  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased activity into one or more parts sold separately.
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On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Key West over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

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  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

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  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.